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H1B Resigning and Stay for Leisure on ESTA (VWP)?

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  • H1B Resigning and Stay for Leisure on ESTA (VWP)?

    I'm a Japanese citizen and I've been working in the US on H1B visa for several years. I came to a decision to move back to my country, so I am prematurely terminating my H1B visa. Now I would like to stay in the US for 14 to 45 days after that just for a leisure purpose and travel within the US (as well as selling furniture, etc).

    There is no grace period for H1B visa holders when their status become invalid as far as I could find out (Called HR, company's law firm, USCIS multiple times).

    One option is to apply for a B-2 visa and make a change status request, which I can only do by mail, and as I've called USCIS, they told me that it won't be processed for months (They are processing ones from October 2015 now) and certainly my application will become void while I won't be out of status. This costs me $290 and not refundable for my case.

    Another option I am considering is to visit Canada on the next day of my last day at work and then reenter the US after a few days. Japan is under the Visa Waiver Program. But my biggest fear is the rejection to re-enter.

    Can I get an ESTA from Canada to reenter the US? Do I need to buy a plane ticket from the US to move back to my country (which I would do beforehand if it makes it safer)?

    Thanks!!

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